ABSTRACT
NMR studies have shown that seven new sesquiterpenoids, 3, 4, 5a, and 7-10, isolated from dried samples of the New Zealand liverwort Lepidolaena hodgsoniae have the same substituted cyclopentapyran ring system as the previously described insecticidal sesquiterpene diene hodgsonox (1), which has been reported only from this plant. In all but one compound, 10, the 1,1-disubstituted double bond of hodgsonox has migrated into an endocyclic position, but only two, 5a and 9, have the double bonds in conjugation. These seven new compounds represent a variety of different oxidation levels. Two of the new derivatives, 9 and 10, were isolated only from an aged sample and are presumably artifacts. The only other terpenoid isolated in significant quantity was (7R,10R)-calamenene (2).
Subject(s)
Hepatophyta/chemistry , Insecticides/isolation & purification , Plants, Medicinal/chemistry , Pyrans/isolation & purification , Sesquiterpenes/isolation & purification , Vinyl Compounds/isolation & purification , Insecticides/chemistry , Insecticides/pharmacology , Molecular Conformation , Molecular Structure , New Zealand , Nuclear Magnetic Resonance, Biomolecular , Polycyclic Sesquiterpenes , Pyrans/chemistry , Pyrans/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Stereoisomerism , Terpenes/chemistry , Terpenes/isolation & purification , Vinyl Compounds/chemistry , Vinyl Compounds/pharmacologyABSTRACT
Five new sacculatane diterpenoids, 17,18-epoxy-7-sacculaten-12,11-olide, 7,17-sacculatadien-11,12-olide, 11beta,12-epoxy-7,17-sacculatadien-11alpha-ol, 1beta-acetoxy-11beta,12-epoxy-7,17-sacculatadien-11alpha-ol and 1beta,15xi-diacetoxy-11,12-epoxy-8(12),9(11),17-sacculatatriene along with sacculatal and sacculatanolide have been isolated from axenic cultures of the liverwort Fossombronia wondraczekii and their structures assigned on the basis of their spectroscopical properties.
Subject(s)
Diterpenes/chemistry , Hepatophyta/chemistry , Molecular Structure , Tissue Culture TechniquesABSTRACT
Six new labdane type diterpenoids, three seco-clerodane diterpenoids, jamesoniellide I, along with the two new jamesoniellides K and L, the sesquiterpene waitziacuminone and a new chlorinated bisbibenzyl, 6,6',10,10',12,12'-hexachloroisoperrottetin A, have been isolated from the liverwort Jamesoniella colorata. Their structures were elucidated by NMR spectroscopy. The absolute configuration of 3-oxo-labda-8(17),13(16),14-triene (1) was established by CD spectroscopy.
